33 Fastest Horses to Ever Win the Kentucky Derby
The Kentucky Derby is, for many horse-racing fans, the pinnacle race of the year. “The Run for the Roses” is the start of the journey toward the elusive Triple Crown — an award a horse achieves by winning the Kentucky Derby, the Preakness and the Belmont Stakes all in one year.
Steeped in tradition that goes back to the first Kentucky Derby in 1875, ladies still don colorful bonnets and hats to the race, and everyone bets on their favorites. Even if the Triple Crown does allude them, winning the Kentucky Derby is a feather in any jockey’s cap. In its 146-year history, the Derby has seen some incredible equine athletes. Here are the 33 fastest Kentucky Derby horses to ever win from 1875 to 2020.
28. Dark Star (Tie)
This list starts off with a five-way tie, starting with Dark Star, who ran the 1953 Kentucky Derby in 2:02.00.
Kauai King (1966), Foolish Pleasure (1975), Genuine Risk (1980), Pleasant Colony (1981) and Unbridled (1990) would also win the Kentucky Derby in the same time years later.
* All times were sourced from Twinspires.
28. Kauai King (Tie)
Sired by the famed Native Dancer, Kauai King won the 1966 Kentucky Derby and the Preakness, failing to win the Triple Crown when he came in fourth at the Belmont Stakes. He led the way the entire time during the Derby but had to fight for the Preakness.
He just wasn’t up for it by the time the Belmont came around. He was the only Maryland-bred horse to ever win the Kentucky Derby.
28. Foolish Pleasure (Tie)
Foolish Pleasure won the 1975 Kentucky Derby, but that’s not why his name is recognizable by millions.
He is best known for being the horse that was pitted against Ruffian, an undefeated filly, in the great match race that ultimately cost her her life.
28. Genuine Risk (Tie)
Genuine Risk won the Kentucky Derby in 1980 and is one of only three fillies (female horses) to do so.
She is also one of only two fillies to compete in all three Triple Crown races.
28. Pleasant Colony (Tie)
The following year, Pleasant Colony won the Kentucky Derby with the same time of 2:02.00.
While he won the first two legs of the American Triple Crown — the Kentucky Derby and the Preakness Stakes — but not the Belmont Stakes.
28. Unbridled (Tie)
When Unbridled retired in 2001, he had earned almost $4.5 million in career earnings.
Of course, one of his many victories included the 1990 Kentucky Derby.
27. I’ll Have Another
I’ll Have Another won the Santa Anita Derby before heading to Kentucky for the Run for the Roses. In the 2012 Kentucky Derby, he was in post 19, a spot that no winner has ever come from.
Yet, a Triple Crown was not in his future. He was pulled from racing in the Belmont Stakes due to a leg injury and was retired from racing.
26. Big Brown
In 2008, racing fans were hopeful for a Triple Crown winner in Big Brown. He had shown commanding promise in his first race in 2007, winning by 11.25 lengths. Though quarter cracks in his hooves kept him out of some races, when he came back in March 2008, he won that race by 12.75 lengths.
At the Kentucky Derby, he drew the No. 20 post, a place no Derby winner has ever come from. Yet, he swept the 2008 Kentucky Derby by 4.75 lengths and the Preakness by five lengths, remaining undefeated. But, after suffering an abscess and yet another quarter crack, he never came back the same. He finished ninth in the Belmont Stakes, and his career of seven wins in eight races was over.
25. Riva Ridge
Just a year before the great Secretariat would shatter the racing scene, his stablemate Riva Ridge happened to win the 1972 Kentucky Derby. He came in third in the Preakness, ruining his chances for a Triple Crown, but came back to win the Preakness.
Riva Ridge was named Champion 2-Year-Old Colt in 1971 and Champion Older Horse in 1973. He lived to be just 16 when he passed away from a heart attack.
21. Twenty Grand (Tie)
The 21st fastest Kentucky Derby Winner is a four-way tie, starting with Twenty Grand, who won the 1931 Kentucky Derby with a time of 2:01.80.
He also gained fame for winning the Kentucky Jockey Club Stakes, setting a track record for the mile at Churchill Downs — the fastest ever run by a 2-year-old.
21. Majestic Prince (Tie)
Majestic Prince was a favorite to win the Triple Crown, especially after his wins in the 1969 Kentucky Derby and the Preakness. Then, trainer John Longden declared he was pulling him from the Belmont due to a slight injury.
But under pressure from his owner, Frank McMahon, the colt was raced anyway. He had a poor performance that lost him his race, and he never returned to racing.
21. Swaps (Tie)
In 1955, Swaps was the horse to beat. In his 15 starts since he began his career in ’54, he had won 11, including the 1955 Kentucky Derby. Nashua came in second, a horse that would be considered his rival and would later beat him in the Washington Park Match Race.
Due to a hoof wall injury, Swaps did not compete in the Preakness or the Belmont Stakes, and both wins went to Nashua. However, Swaps would come back and win the Santa Anita Handicap in ’56, along with seven others of his 10 starts that year before retiring.
21. Chateaugay (Tie)
Like many before and after him, Chateaugay was denied his Triple Crown by one race. In his case, it was the Preakness. He won both the 1963 Kentucky Derby and the Belmont Stakes. But what really made the Kentucky-bred colt infamous was the fact that he probably would have never run if he had not had a ventriculectomy as a 2-year-old, a surgery that improved his breathing.
At the time, this surgery was not done often, and he was the first future classic winner to have it done. He is also the son of Swaps, who won the 1955 Kentucky Derby. More amazing is that father and son ran the race in the exact same time, 2:01.80.
18. Middleground (Tie)
Middleground came from Texas, the King Ranch in fact. He is one of only two Kentucky Derby winners to hail from the state. Although the King Ranch was famed for its Quarter Horses, they also owned the other Texas-bred Kentucky Derby winner, Assault, who won the Triple Crown in 1946.
Middleground won the 1950 Kentucky Derby, with a time of 2:01.60, which would later be matched by Hill Gail and Bold Forbes. He went on to lose the Preakness to Hill Prince, who beat Middleground in five of their six races together. His racing career was cut short due to an injury, but in his short career, he was only out of the money once.
18. Hill Gail (Tie)
Although Hill Gail was a leading 2-year-old colt when he stepped into the starting gate at the 1952 Kentucky Derby, that race would be his last great triumph. He won by five lengths, but he injured his leg in the race and would never run the same again.
He is one of only five horses to win both the Kentucky Derby and the Derby Trial, where he set a record with a time of 1:35.60.
18. Bold Forbes (Tie)
Before running for the roses, this Kentucky Derby winner was named the Champion Two-Year-Old in Puerto Rico in 1975. Then, in 1976, Bold Forbes would capture both the Kentucky Derby and the Belmont Stakes.
In between them, he came in third at the Preakness, ruining his chance at a Triple Crown. He died in 2000 at 27, making him the oldest living Kentucky Derby winner to date.
Whirlaway not only won the 1941 Kentucky Derby, but he went on to become a Triple Crown winner. But he wasn’t done. He then won the Travers Stakes, becoming the first and only horse to win all four races.
The day before the Kentucky Derby, his trainer cut away the horse’s left blinker, hoping it would stop the erratic behavior the colt was prone to. It may have been that, or maybe the rider change, that led to him sweeping the Triple Crown. He was originally buried in Normandy, France but was moved to Kentucky and is now buried at Calumet, his owner’s farm.
The great Barbaro has a tragic story that many in racing know all too well. He quickly won over fans by winning all the races he ran leading up to the 2016 Kentucky Derby. He was given a five-week break before the big race, the first horse in over 50 years to have that long of a break before the Derby.
He was the second favorite to win and did so with gusto, leading by 6.5 lengths. Unfortunately, in the Preakness, he shattered his leg, which would eventually be the cause for his euthanasia.
In 2016, Nyquist headed to the starting gate as an unbeaten colt. The 2016 Kentucky Derby would not change this, and he became the eighth undefeated Derby winner. He would go on to run as a 3-year-old, breaking his winning streak, finally. He won eight of his 11 career starts.
Before his Derby run, he won the 2015 Breeders' Cup Juvenile, becoming only the second horse in history to win both races.
12. Lucky Debonair (Tie)
Lucky Debonair is a Kentucky-grown colt that first made a splash in the racing scene when he won the Santa Anita Derby in a record-winning 1:47 flat. He still holds that record, shared with Sham (1973) and Indian Charlie (1998).
He went on to win the 1965 Kentucky Derby with a time of 2:01.20, which he shares with Affirmed and Thunder Gulch.
12. Affirmed (Tie)
Affirmed is one of those racehorses that, decades later, anyone that even casually watches racing knows. He won the 1978 Kentucky Derby and then went on to capture the Triple Crown.
His overall career was spectacular, winning 22 of 29 races. In his first race, he led gate to wire and won by 4.5 lengths. He was named Horse of the Year in 1979.
12. Thunder Gulch (Tie)
In 1995, Thunder Gulch would win the Kentucky Derby with a time of 2:01.20. He would go on to place a disappointing third in the Preakness but come back to win the Belmont Stakes. These wins, along with the Florida Derby and the Travers Stakes, garnered him the U.S. Champion Three-Year-Old Colt award for the year.
Owned by Michael Tabor, he lived to the ripe old age of 26.
11. Funny Cide
Funny Cide, like War Emblem, made a valiant effort towards Triple Crown Glory. He won the 2003 Kentucky Derby with a fast 2:01.19 time and then went on to win the Preakness with a time of 1:55.61. However, he, too, was beaten in the Belmont Stakes, by Empire Maker, the second-place winner of the Kentucky Derby.
Funning Cide was bred in New York and owned by Sackatoga Stable, making him only the second horse bred in New York to win the Derby — the first was Clyde Van Dusen in 1929.
10. War Emblem
War Emblem, a gorgeous black stallion, was a favorite in the hearts of many racing fans. Purchased by Prince Ahmed Bin Salman of Saudi Arabia just three weeks before the Kentucky Derby, he was transferred to the famous Bob Baffert’s training barn.
His Kentucky Derby performance was astonishing — he led the entire time, from gate to wire, and won by four lengths. He went on to win the Preakness but stumbled at the start of the Belmont Stakes, costing him the Triple Crown.
8. Fusaichi Pegasus (Tie)
Fusaichi Pegasus was sired by Mr. Prospector, a stallion whose name appears on the lineage of 51 Kentucky Derby winners. He was purchased by Fusao Sekiguchi, a Japanese businessman, at a yearling sale for $4 million, making him the most expensive horse at the sale.
In 2000, he earned his worth by winning the three big races at Santa Anita and then the Kentucky Derby. He was the first favorite to win the Derby since 1979.
8. Grindstone (Tie)
Owned by Overbrook Farm, Grindstone won the 1996 Kentucky Derby after running in just two other races, neither of which he won. Winning by just a nose, he never raced again.
Now retired, he was the only Derby winner to ever stand at stud in the Northwest United States. One of his offspring, Birdstone, won the Belmont Stakes in 2004.
Last year, in 2020, Authentic would become the first horse since 2003 to break the top 10 fastest Kentucky Derby winners list, with a time of 2:00.61. He is owned by Silverton Hill LLC and was named Horse of the Year in 2020 as well.
It was also the year that, for the first time, the Kentucky Derby was run in September instead of May due to COVID-19. This incredible stallion is also distantly related to the famous Ruffian.
6. Proud Clarion
Proud Clarion was a Kentucky-bred and -owned stallion who won the Kentucky Derby in 1967. His owner/breeder was John Galbreath.
Proud Clarion was the longshot of the race, with 30:1 odds, with a non-stellar racing career up to that point. Although he won a few other skate races, the Derby was definitely the bright spot in his career.
Decidedly was the son of Determine, who had won the Kentucky Derby in 1954, with the 58th fastest time of 2:03.00, .02 seconds faster than American Pharoah.
Outrunning his father, Decidedly won the Kentucky Derby in 1962 in just 2:00.40. He was bred in California by George Pope.
4. Spend A Buck
Spend A Buck was owned by Hunter Farms (Dennis Diaz). In 1985, he won the Kentucky Derby in just over two minutes. Diaz made a choice that year to not run him in the Preakness or the Belmont Stakes because Garden State Park had offered a special award of $2 million to a horse that could win the Cherry Hill Mile, Garden State Skates, Kentucky Derby and Jersey Derby.
Since the Jersey Derby was held after the Kentucky Derby, Diaz did not want to enter Spend A Buck in the Preakness or the Belmont Stake, but instead saved him for the Jersey Derby.
3. Northern Dancer
Northern Dancer won the 1964 Kentucky Derby in two minutes flat. But his real claim to fame was being the first Canadian-bred horse to win the Derby.
Owned by E.P. Taylor, Northern Dancer was bred in Oshawa, Ontario. He won the Preakness but placed third in the Belmont Stakes.
Monarchos won the Kentucky Derby in 2001 in just under two minutes, making him the second horse to ever win with a time that fast, right on the heels of the famed Secretariat.
The gorgeous grey stallion only ran 10 times in his career, and only won four of those starts, but he definitely made his mark. He was owned by John C. Oxley and passed away in 2016.
In 1973, a big red horse put on a show, the likes of which we will probably never see again. Owned by Penny Chenery, Secretariat won the Kentucky Derby at a blinding speed of 1:59.40. His record has never been broken.
That year, he went on to win the Triple Crown, with an incredible, 31 horse-length lead in the Belmont Stakes.